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[dankir]

The first time I had sex with my first girlfriend definitely takes the cake. We were at my house watching TV and getting drunk, and all the sudden I was hammering away on top of her. It was going great until she was on top of me, and while bouncing around realized I had gone semi-limp and the condom no where to be seen. She was pretty insecure so I didn't want to tell her I had gone limp inside of her, so in panic-mode I said I had came.

All hell broke loose. She began screaming at me and that subsided into her crying on my floor, naked. I told her I'd buy a Plan B the next day, and that seemed to calm things down. After about 5 minutes of awkward bouts of conversation, her friend called and she soon left to see said friend - who was a guy.

This really seemed to have scared her away from sex, at least with me, because we rarely had sex after that and the relationship would end four months later. Ah, to be young and inexperienced.

Sorry I LOL'D

 

[Zampano]

Slept with a fatty with one tit bigger than the other. Couldn't finish as she was a hosebeast so kept pounding. Snapped my banjo string. Didn't realise at the time as I was wasted until she went down and got a mouthful of blood.

 

[Dr_Boris_Goltz]

Ahh, interesting. thanks. One more thing I've always wondered though, so I hope you don't mind my asking... does it make you diamond cutting rock hard the entire time, or does it kind of bounce between that and just, like, regular old hard?

It's actually always maxed out. In fact, it gives me the strongest erections I have ever experienced.

When I say robotic I truly mean it. This is how I imagine Gigolo Joe's penis works.

 

[mackattk]

Slept with a fatty with one tit bigger than the other. Couldn't finish as she was a hosebeast so kept pounding. Snapped my banjo string. Didn't realise at the time as I was wasted until she went down and got a mouthful of blood.

Out of everything that I have read in this thread, this one made me shudder. OUCH

 

[FairyD]

Slept with a fatty with one tit bigger than the other. Couldn't finish as she was a hosebeast so kept pounding. Snapped my banjo string. Didn't realise at the time as I was wasted until she went down and got a mouthful of blood.

I don't understand. Did you burst a blood vessel or something?

 

[Danneee]

Picked up some girl from work one night. Went to her place but she had a ferret running around biting me, she did put it in a closet later but needless to say I had to fake it.
Comforted myself the next day by buying an iPad

 

[Ciastek3214]

I don't understand. Did you burst a blood vessel or something?

Probably. Happens more often than you think.

 

[Nekofrog]

I don't understand. Did you burst a blood vessel or something?

Look at the underside of your cock. See that skin connecting the hood to the base of the head of your dick? That thing.

Same thing happened to me and my wife when we were dating, only I was dropping a load in her when she pulled me in and it broke like an tightly wound guitar string.

blood.fucking.everywhere.

 

[andymcc]

i think i posted this story in an other thread before, but, the worst sex i ever had was the first time. not only was it bad sex, the circumstances following the sex are so fucking bizarre too.

there was this girl i sorta had a crush on throughout a significant period of high school. she had a boyfriend that was significantly older, like four or five years iirc, so i figured that it would never amount to anything. she had pretty good taste in music, and she was always pretty flirtatious whenever she'd see me at lunch (we sat at the same table).

her long-term boyfriend and her split for unknown reasons and, almost immediately after this happening, a mutual friend of the two of us informs me that the girl i crushed on wants to go to homecoming with me. i asked her, she said yes.

a few days after saying yes, she asks if she can come over (she only lived a few blocks away) and watch some movies. i knew exactly what that meant so, of course, i said yes. we made out pretty hot and heavy, etc. etc. but nothing past that.

the following week was homecoming. we left the dance early to go back to my place. i lived at my dad's house at this time, and he worked the night shift this particular evening... or so i thought.

we're in my basement, where i lived at the time, we start making out, one thing leads to another and we're naked. i slip on the condom and after 45 seconds of awkward thrusting, i'm done.

i told her of my premature ejaculation. she wasn't amused.

i hear my dad loudly enter the house upstairs and now we both were equally unamused.

"andy, andy, help me unload groceries!" i hear him call at the top of the stairs.

hurriedly, without slipping the condom off, i do just that. very quickly putting groceries in their respective areas while the naked girl on my bed sits there, probably becoming increasingly frustrated by every passing second.

i descend the stairs, apologizing profusely. she seems pretty perturbed, understandably so. i realize that something else was amiss here, and begin to pat my crotch, noticing the condom wasn't there.

after telling her the condom came off at some point between the bed and being upstairs, the girl starts crying. not only was she probably frustrated by the sex, but what great circumstances to meet my dad for the first time under. i frantically search the floor in hopes that it just fell off while i was putting my slacks on but then--

"Andy! Andy!" my dad exclaimed again, sounding less than chipper.

I rush upstairs and my dad tells me, "Andy, you won't believe what I found..."

"what?" I didn't want to guess, I just knew...

"A rubber snake."

My heart dropped. I've been found out.

"What?"

"A rubber snake!" and my dad, who has always been quite the prankster, throws an honest-to-god toy rubber snake at me.

I groaned loudly and stormed off, probably unaware of why I was so frustrated with him.

Back in the basement, the girl is still crying. I notice on the floor, right beside one of the legs of the bed, there it was... the used condom. I laughed, she didn't.

A few days later she would break up with me. We never really spoke again after that.

 

[JaseMath]

I met this girl on MySpace a few years back. She was gorgeous, but my god, she was violent in bed. My back, the back of my arms, and my ass had deep scratches in them for weeks. My bedsheets looked like the Shroud of Turin.

 

[Jo Shishido's Cheeks]

So this girl I was with finally granted me permission for some anal lovage.
I'm warming up her ass with a vibrator, slowly pushing it to and fro with my left hand whilst playing with her pussy with the right, two fingers in and my thumb working her clit.
She's getting very excited by what my right hand is doing, so I momentarily lose focus of the careful actions of my left hand.

"Ploop."

The vibrator disappears up her ass.
No biggie I figure, I can just dig it out.
So I reach in deeper with my left hand whilst stopping what I'm doing with my right.

"What are you doing?"
".....Oh nothing just grabbing this thing."
"What!?"

She leaps up off the bed and begins to panic. I sit her back down, explain, make a couple of jokes and begin my second excavation attempt.
The problem now is between her getting up and sitting back down it's become lodged in at a strange angle and seemingly won't come out.
I pull firmly.
A sudden warm sensation.
Blood.
Lots of blood.

She runs to the toilet, leaking blood over my cream carpet whilst I run after her beginning to freak. I don't like the sight of blood.
She sits on the toilet and begins having what sounds like a very heavy, manly piss.
I look into the toilet and it looks like a prop bucket from Carrie.
So much blood.
I'm trying my hardest to pull this vibrator out but it won't budge.
The blood is making my attempt to get a decent grip on it difficult.
She's crying.
I suggest going to hospital to remove it and she cries more, shouting at me for thinking of putting her in the situation of explaining to the doctor what's wrong.

After a huge amount of blood (repeated flushes were needed), tears and struggles I finally wrestle this vibrator from her ass.
It's still on and vibrating happily.

The downside is this experience has put me off from ever attempting anal sex again.
The upside is I kept the vibrator and gave it to her as a gift a few months later.
She smiled.

 

[joedan]

So this girl I was with finally granted me permission for some anal lovage.
I'm warming up her ass with a vibrator, slowly pushing it to and fro with my left hand whilst playing with her pussy with the right, two fingers in and my thumb working her clit.
She's getting very excited by what my right hand is doing, so I momentarily lose focus of the careful actions of my left hand.

"Ploop."

The vibrator disappears up her ass.
No biggie I figure, I can just dig it out.
So I reach in deeper with my left hand whilst stopping what I'm doing with my right.

"What are you doing?"
".....Oh nothing just grabbing this thing."
"What!?"

She leaps up off the bed and begins to panic. I sit her back down, explain, make a couple of jokes and begin my second excavation attempt.
The problem now is between her getting up and sitting back down it's become lodged in at a strange angle and seemingly won't come out.
I pull firmly.
A sudden warm sensation.
Blood.
Lots of blood.

She runs to the toilet, leaking blood over my cream carpet whilst I run after her beginning to freak. I don't like the sight of blood.
She sits on the toilet and begins having what sounds like a very heavy, manly piss.
I look into the toilet and it looks like a prop bucket from Carrie.
So much blood.
I'm trying my hardest to pull this vibrator out but it won't budge.
The blood is making my attempt to get a decent grip on it difficult.
She's crying.
I suggest going to hospital to remove it and she cries more, shouting at me for thinking of putting her in the situation of explaining to the doctor what's wrong.

After a huge amount of blood (repeated flushes were needed), tears and struggles I finally wrestle this vibrator from her ass.
It's still on and vibrating happily.

The downside is this experience has put me off from ever attempting anal sex again.
The upside is I kept the vibrator and gave it to her as a gift a few months later.
She smiled.

Wow. LOL

 

[BFIB]

So this girl I was with finally granted me permission for some anal lovage.
I'm warming up her ass with a vibrator, slowly pushing it to and fro with my left hand whilst playing with her pussy with the right, two fingers in and my thumb working her clit.
She's getting very excited by what my right hand is doing, so I momentarily lose focus of the careful actions of my left hand.

"Ploop."

The vibrator disappears up her ass.
No biggie I figure, I can just dig it out.
So I reach in deeper with my left hand whilst stopping what I'm doing with my right.

"What are you doing?"
".....Oh nothing just grabbing this thing."
"What!?"

She leaps up off the bed and begins to panic. I sit her back down, explain, make a couple of jokes and begin my second excavation attempt.
The problem now is between her getting up and sitting back down it's become lodged in at a strange angle and seemingly won't come out.
I pull firmly.
A sudden warm sensation.
Blood.
Lots of blood.

She runs to the toilet, leaking blood over my cream carpet whilst I run after her beginning to freak. I don't like the sight of blood.
She sits on the toilet and begins having what sounds like a very heavy, manly piss.
I look into the toilet and it looks like a prop bucket from Carrie.
So much blood.
I'm trying my hardest to pull this vibrator out but it won't budge.
The blood is making my attempt to get a decent grip on it difficult.
She's crying.
I suggest going to hospital to remove it and she cries more, shouting at me for thinking of putting her in the situation of explaining to the doctor what's wrong.

After a huge amount of blood (repeated flushes were needed), tears and struggles I finally wrestle this vibrator from her ass.
It's still on and vibrating happily.

The downside is this experience has put me off from ever attempting anal sex again.
The upside is I kept the vibrator and gave it to her as a gift a few months later.
She smiled.

Close this thread. This is the winner.

 

[cjkeats]

I'm in tears. That's amazing

 

[Sallokin]

Look at the underside of your cock. See that skin connecting the hood to the base of the head of your dick? That thing.

Same thing happened to me and my wife when we were dating, only I was dropping a load in her when she pulled me in and it broke like an tightly wound guitar string.

blood.fucking.everywhere.

This just sounds crazy. I've had torn skin before, but that sounds like the ultimate nightmare.

 

[Dreams-Visions]

Worst?

Beautiful girl. Horrible lay, man. Just horrible. With an odor I'd soon forget if I could but can't.

So this girl I was with finally granted me permission for some anal lovage.
I'm warming up her ass with a vibrator, slowly pushing it to and fro with my left hand whilst playing with her pussy with the right, two fingers in and my thumb working her clit.
She's getting very excited by what my right hand is doing, so I momentarily lose focus of the careful actions of my left hand.

"Ploop."

The vibrator disappears up her ass.
No biggie I figure, I can just dig it out.
So I reach in deeper with my left hand whilst stopping what I'm doing with my right.

"What are you doing?"
".....Oh nothing just grabbing this thing."
"What!?"

She leaps up off the bed and begins to panic. I sit her back down, explain, make a couple of jokes and begin my second excavation attempt.
The problem now is between her getting up and sitting back down it's become lodged in at a strange angle and seemingly won't come out.
I pull firmly.
A sudden warm sensation.
Blood.
Lots of blood.

She runs to the toilet, leaking blood over my cream carpet whilst I run after her beginning to freak. I don't like the sight of blood.
She sits on the toilet and begins having what sounds like a very heavy, manly piss.
I look into the toilet and it looks like a prop bucket from Carrie.
So much blood.
I'm trying my hardest to pull this vibrator out but it won't budge.
The blood is making my attempt to get a decent grip on it difficult.
She's crying.
I suggest going to hospital to remove it and she cries more, shouting at me for thinking of putting her in the situation of explaining to the doctor what's wrong.

After a huge amount of blood (repeated flushes were needed), tears and struggles I finally wrestle this vibrator from her ass.
It's still on and vibrating happily.

The downside is this experience has put me off from ever attempting anal sex again.
The upside is I kept the vibrator and gave it to her as a gift a few months later.
She smiled.

mother of god.

 

[andymcc]

So this girl I was with finally granted me permission for some anal lovage.
I'm warming up her ass with a vibrator, slowly pushing it to and fro with my left hand whilst playing with her pussy with the right, two fingers in and my thumb working her clit.
She's getting very excited by what my right hand is doing, so I momentarily lose focus of the careful actions of my left hand.

"Ploop."

The vibrator disappears up her ass.
No biggie I figure, I can just dig it out.
So I reach in deeper with my left hand whilst stopping what I'm doing with my right.

"What are you doing?"
".....Oh nothing just grabbing this thing."
"What!?"

She leaps up off the bed and begins to panic. I sit her back down, explain, make a couple of jokes and begin my second excavation attempt.
The problem now is between her getting up and sitting back down it's become lodged in at a strange angle and seemingly won't come out.
I pull firmly.
A sudden warm sensation.
Blood.
Lots of blood.

She runs to the toilet, leaking blood over my cream carpet whilst I run after her beginning to freak. I don't like the sight of blood.
She sits on the toilet and begins having what sounds like a very heavy, manly piss.
I look into the toilet and it looks like a prop bucket from Carrie.
So much blood.
I'm trying my hardest to pull this vibrator out but it won't budge.
The blood is making my attempt to get a decent grip on it difficult.
She's crying.
I suggest going to hospital to remove it and she cries more, shouting at me for thinking of putting her in the situation of explaining to the doctor what's wrong.

After a huge amount of blood (repeated flushes were needed), tears and struggles I finally wrestle this vibrator from her ass.
It's still on and vibrating happily.

The downside is this experience has put me off from ever attempting anal sex again.
The upside is I kept the vibrator and gave it to her as a gift a few months later.
She smiled.

oh my god

 

[Baron Doggystyle von Woof]

So this girl I was with finally granted me permission for some anal lovage.
I'm warming up her ass with a vibrator, slowly pushing it to and fro with my left hand whilst playing with her pussy with the right, two fingers in and my thumb working her clit.
She's getting very excited by what my right hand is doing, so I momentarily lose focus of the careful actions of my left hand.

"Ploop."

The vibrator disappears up her ass.
No biggie I figure, I can just dig it out.
So I reach in deeper with my left hand whilst stopping what I'm doing with my right.

"What are you doing?"
".....Oh nothing just grabbing this thing."
"What!?"

She leaps up off the bed and begins to panic. I sit her back down, explain, make a couple of jokes and begin my second excavation attempt.
The problem now is between her getting up and sitting back down it's become lodged in at a strange angle and seemingly won't come out.
I pull firmly.
A sudden warm sensation.
Blood.
Lots of blood.

She runs to the toilet, leaking blood over my cream carpet whilst I run after her beginning to freak. I don't like the sight of blood.
She sits on the toilet and begins having what sounds like a very heavy, manly piss.
I look into the toilet and it looks like a prop bucket from Carrie.
So much blood.
I'm trying my hardest to pull this vibrator out but it won't budge.
The blood is making my attempt to get a decent grip on it difficult.
She's crying.
I suggest going to hospital to remove it and she cries more, shouting at me for thinking of putting her in the situation of explaining to the doctor what's wrong.

After a huge amount of blood (repeated flushes were needed), tears and struggles I finally wrestle this vibrator from her ass.
It's still on and vibrating happily.

The downside is this experience has put me off from ever attempting anal sex again.
The upside is I kept the vibrator and gave it to her as a gift a few months later.
She smiled.

 

[Shin Johnpv]

So you fucked Bane?

When Gotham is in ashes, you have my permission to cum.

 

[Blue Ninja]

The tale of the magically disappearing vibrator.

We have a winner, folks.

 

[MrOogieBoogie]

So this girl I was with finally granted me permission for some anal lovage.
I'm warming up her ass with a vibrator, slowly pushing it to and fro with my left hand whilst playing with her pussy with the right, two fingers in and my thumb working her clit.
She's getting very excited by what my right hand is doing, so I momentarily lose focus of the careful actions of my left hand.

"Ploop."

The vibrator disappears up her ass.
No biggie I figure, I can just dig it out.
So I reach in deeper with my left hand whilst stopping what I'm doing with my right.

"What are you doing?"
".....Oh nothing just grabbing this thing."
"What!?"

She leaps up off the bed and begins to panic. I sit her back down, explain, make a couple of jokes and begin my second excavation attempt.
The problem now is between her getting up and sitting back down it's become lodged in at a strange angle and seemingly won't come out.
I pull firmly.
A sudden warm sensation.
Blood.
Lots of blood.

She runs to the toilet, leaking blood over my cream carpet whilst I run after her beginning to freak. I don't like the sight of blood.
She sits on the toilet and begins having what sounds like a very heavy, manly piss.
I look into the toilet and it looks like a prop bucket from Carrie.
So much blood.
I'm trying my hardest to pull this vibrator out but it won't budge.
The blood is making my attempt to get a decent grip on it difficult.
She's crying.
I suggest going to hospital to remove it and she cries more, shouting at me for thinking of putting her in the situation of explaining to the doctor what's wrong.

After a huge amount of blood (repeated flushes were needed), tears and struggles I finally wrestle this vibrator from her ass.
It's still on and vibrating happily.

The downside is this experience has put me off from ever attempting anal sex again.
The upside is I kept the vibrator and gave it to her as a gift a few months later.
She smiled.

 

[JohnDoe]

So this girl I was with finally granted me permission for some anal lovage.
I'm warming up her ass with a vibrator, slowly pushing it to and fro with my left hand whilst playing with her pussy with the right, two fingers in and my thumb working her clit.
She's getting very excited by what my right hand is doing, so I momentarily lose focus of the careful actions of my left hand.

"Ploop."

The vibrator disappears up her ass.
No biggie I figure, I can just dig it out.
So I reach in deeper with my left hand whilst stopping what I'm doing with my right.

"What are you doing?"
".....Oh nothing just grabbing this thing."
"What!?"

She leaps up off the bed and begins to panic. I sit her back down, explain, make a couple of jokes and begin my second excavation attempt.
The problem now is between her getting up and sitting back down it's become lodged in at a strange angle and seemingly won't come out.
I pull firmly.
A sudden warm sensation.
Blood.
Lots of blood.

She runs to the toilet, leaking blood over my cream carpet whilst I run after her beginning to freak. I don't like the sight of blood.
She sits on the toilet and begins having what sounds like a very heavy, manly piss.
I look into the toilet and it looks like a prop bucket from Carrie.
So much blood.
I'm trying my hardest to pull this vibrator out but it won't budge.
The blood is making my attempt to get a decent grip on it difficult.
She's crying.
I suggest going to hospital to remove it and she cries more, shouting at me for thinking of putting her in the situation of explaining to the doctor what's wrong.

After a huge amount of blood (repeated flushes were needed), tears and struggles I finally wrestle this vibrator from her ass.
It's still on and vibrating happily.

The downside is this experience has put me off from ever attempting anal sex again.
The upside is I kept the vibrator and gave it to her as a gift a few months later.
She smiled.

... FUCK

 

[DukeBobby]

So this girl I was with finally granted me permission for some anal lovage.
I'm warming up her ass with a vibrator, slowly pushing it to and fro with my left hand whilst playing with her pussy with the right, two fingers in and my thumb working her clit.
She's getting very excited by what my right hand is doing, so I momentarily lose focus of the careful actions of my left hand.

"Ploop."

The vibrator disappears up her ass.
No biggie I figure, I can just dig it out.
So I reach in deeper with my left hand whilst stopping what I'm doing with my right.

"What are you doing?"
".....Oh nothing just grabbing this thing."
"What!?"

She leaps up off the bed and begins to panic. I sit her back down, explain, make a couple of jokes and begin my second excavation attempt.
The problem now is between her getting up and sitting back down it's become lodged in at a strange angle and seemingly won't come out.
I pull firmly.
A sudden warm sensation.
Blood.
Lots of blood.

She runs to the toilet, leaking blood over my cream carpet whilst I run after her beginning to freak. I don't like the sight of blood.
She sits on the toilet and begins having what sounds like a very heavy, manly piss.
I look into the toilet and it looks like a prop bucket from Carrie.
So much blood.
I'm trying my hardest to pull this vibrator out but it won't budge.
The blood is making my attempt to get a decent grip on it difficult.
She's crying.
I suggest going to hospital to remove it and she cries more, shouting at me for thinking of putting her in the situation of explaining to the doctor what's wrong.

After a huge amount of blood (repeated flushes were needed), tears and struggles I finally wrestle this vibrator from her ass.
It's still on and vibrating happily.

The downside is this experience has put me off from ever attempting anal sex again.
The upside is I kept the vibrator and gave it to her as a gift a few months later.
She smiled.

 

[BFIB]

So this girl I was with finally granted me permission for some anal lovage.
I'm warming up her ass with a vibrator, slowly pushing it to and fro with my left hand whilst playing with her pussy with the right, two fingers in and my thumb working her clit.
She's getting very excited by what my right hand is doing, so I momentarily lose focus of the careful actions of my left hand.

"Ploop."

The vibrator disappears up her ass.
No biggie I figure, I can just dig it out.
So I reach in deeper with my left hand whilst stopping what I'm doing with my right.

"What are you doing?"
".....Oh nothing just grabbing this thing."
"What!?"

She leaps up off the bed and begins to panic. I sit her back down, explain, make a couple of jokes and begin my second excavation attempt.
The problem now is between her getting up and sitting back down it's become lodged in at a strange angle and seemingly won't come out.
I pull firmly.
A sudden warm sensation.
Blood.
Lots of blood.

She runs to the toilet, leaking blood over my cream carpet whilst I run after her beginning to freak. I don't like the sight of blood.
She sits on the toilet and begins having what sounds like a very heavy, manly piss.
I look into the toilet and it looks like a prop bucket from Carrie.
So much blood.
I'm trying my hardest to pull this vibrator out but it won't budge.
The blood is making my attempt to get a decent grip on it difficult.
She's crying.
I suggest going to hospital to remove it and she cries more, shouting at me for thinking of putting her in the situation of explaining to the doctor what's wrong.

After a huge amount of blood (repeated flushes were needed), tears and struggles I finally wrestle this vibrator from her ass.
It's still on and vibrating happily.

The downside is this experience has put me off from ever attempting anal sex again.
The upside is I kept the vibrator and gave it to her as a gift a few months later.
She smiled.

Shitception

 

[Omegasquash]

i think i posted this story in an other thread before, but, the worst sex i ever had was the first time. not only was it bad sex, the circumstances following the sex are so fucking bizarre too.

there was this girl i sorta had a crush on throughout a significant period of high school. she had a boyfriend that was significantly older, like four or five years iirc, so i figured that it would never amount to anything. she had pretty good taste in music, and she was always pretty flirtatious whenever she'd see me at lunch (we sat at the same table).

her long-term boyfriend and her split for unknown reasons and, almost immediately after this happening, a mutual friend of the two of us informs me that the girl i crushed on wants to go to homecoming with me. i asked her, she said yes.

a few days after saying yes, she asks if she can come over (she only lived a few blocks away) and watch some movies. i knew exactly what that meant so, of course, i said yes. we made out pretty hot and heavy, etc. etc. but nothing past that.

the following week was homecoming. we left the dance early to go back to my place. i lived at my dad's house at this time, and he worked the night shift this particular evening... or so i thought.

we're in my basement, where i lived at the time, we start making out, one thing leads to another and we're naked. i slip on the condom and after 45 seconds of awkward thrusting, i'm done.

i told her of my premature ejaculation. she wasn't amused.

i hear my dad loudly enter the house upstairs and now we both were equally unamused.

"andy, andy, help me unload groceries!" i hear him call at the top of the stairs.

hurriedly, without slipping the condom off, i do just that. very quickly putting groceries in their respective areas while the naked girl on my bed sits there, probably becoming increasingly frustrated by every passing second.

i descend the stairs, apologizing profusely. she seems pretty perturbed, understandably so. i realize that something else was amiss here, and begin to pat my crotch, noticing the condom wasn't there.

after telling her the condom came off at some point between the bed and being upstairs, the girl starts crying. not only was she probably frustrated by the sex, but what great circumstances to meet my dad for the first time under. i frantically search the floor in hopes that it just fell off while i was putting my slacks on but then--

"Andy! Andy!" my dad exclaimed again, sounding less than chipper.

I rush upstairs and my dad tells me, "Andy, you won't believe what I found..."

"what?" I didn't want to guess, I just knew...

"A rubber snake."

My heart dropped. I've been found out.

"What?"

"A rubber snake!" and my dad, who has always been quite the prankster, throws an honest-to-god toy rubber snake at me.

I groaned loudly and stormed off, probably unaware of why I was so frustrated with him.

Back in the basement, the girl is still crying. I notice on the floor, right beside one of the legs of the bed, there it was... the used condom. I laughed, she didn't.

A few days later she would break up with me. We never really spoke again after that.

First time is a great time for the earlier referenced whiskey dick. Longer lasting, mind bogglingly awesome. I tip my hat to you, sir. That's a SMH moment if ever I've read one.

 

[Yager]

Wonder how many of you guys were also your ladies' worst sexual experience.

Yeah, well, that's not what we are discussing.

 

[andymcc]

First time is a great time for the earlier referenced whiskey dick. Longer lasting, mind bogglingly awesome. I tip my hat to you, sir. That's a SMH moment if ever I've read one.

i was 17 and, back then, i was in my Fugazi straight-edge anti-drug mode.

 

[Artanisix]

So I get there and she has picked out 4 crappy movies and equally crappy food...ok bad start.....Let me just go get a beer......d'oh........fruit juice? WTF? Are we 21 or 16?

I tolerate an entire weekend of immensely boring conversation about politics and school shit and manage to avoid 3 awesome parties that I distinctly remember because all I ever heard about was how it was like 3-1 girls to guys and crazy epic legendary shit went down (in one of them some people managed to destroy a 200 foot long chain link fence.....with a lawnmower....d'oh)

Anyway, finally we get to the point where I know I am getting laid and......yup.....she lays there better than any corpse in any movie I have ever seen while trying to TALK ABOUT SCHOOLWORK while I am getting my dinky do on......

To top it off after 5 minutes she says "you're too thick you're hurting me, let's stop"

I found a reason to leave, can't remember why, and never spoke to her again. Truthfully I wasn't even mad we stopped. I was glad to GTFO of that shit.

...My girlfriend and I like to drink juice when fucking around... especially Kern's Strawberry Banana juice. Goddamn that stuff is good.

Also it doesn't sound like you were "too thick" (don't get your hopes up), sounds more like she was completely disinterested in you and wasn't even turned on. Also sounds like you did zero foreplay to get her to open up. Like, the other posters in this thread have legitimate reasons for bad lays... but this one? Come on now, you were the bad lay here, not the girl.

 

[PwnCakes193]

So this girl I was with finally granted me permission for some anal lovage.
I'm warming up her ass with a vibrator, slowly pushing it to and fro with my left hand whilst playing with her pussy with the right, two fingers in and my thumb working her clit.
She's getting very excited by what my right hand is doing, so I momentarily lose focus of the careful actions of my left hand.

"Ploop."

The vibrator disappears up her ass.
No biggie I figure, I can just dig it out.
So I reach in deeper with my left hand whilst stopping what I'm doing with my right.

"What are you doing?"
".....Oh nothing just grabbing this thing."
"What!?"

She leaps up off the bed and begins to panic. I sit her back down, explain, make a couple of jokes and begin my second excavation attempt.
The problem now is between her getting up and sitting back down it's become lodged in at a strange angle and seemingly won't come out.
I pull firmly.
A sudden warm sensation.
Blood.
Lots of blood.

She runs to the toilet, leaking blood over my cream carpet whilst I run after her beginning to freak. I don't like the sight of blood.
She sits on the toilet and begins having what sounds like a very heavy, manly piss.
I look into the toilet and it looks like a prop bucket from Carrie.
So much blood.
I'm trying my hardest to pull this vibrator out but it won't budge.
The blood is making my attempt to get a decent grip on it difficult.
She's crying.
I suggest going to hospital to remove it and she cries more, shouting at me for thinking of putting her in the situation of explaining to the doctor what's wrong.

After a huge amount of blood (repeated flushes were needed), tears and struggles I finally wrestle this vibrator from her ass.
It's still on and vibrating happily.

The downside is this experience has put me off from ever attempting anal sex again.
The upside is I kept the vibrator and gave it to her as a gift a few months later.
She smiled.

Oh wow. I can't stop laughing... this is incredible. The amount of WTF this post generates is amazing.

 

[Red]

Slept with a fatty with one tit bigger than the other. Couldn't finish as she was a hosebeast so kept pounding. Snapped my banjo string. Didn't realise at the time as I was wasted until she went down and got a mouthful of blood.

o god why

 

[Anaslex]

I was having drunk sex one time and after a bit, i realized that it was starting to hurt my dick a bit. Turned on the light and noticed a bit of blood from my dick and a the end of a string coming out of her vagina. Realized we never removed the tampon before doing it.

Moral of the story? Always eat pussy!

 

[Omegasquash]

i was 17 and, back then, i was in my Fugazi straight-edge anti-drug mode.

Oof. Don't worry man, I was 20 for my first, with a swagger that was chemically induced and I still only lasted a few minutes.

 

[Newline]

Has to be this one night stand I had with this hungarian girl. She just laid there in missionary position like a corpse, it wasn't even like she was limp or anything, I tried moving her around, picking her up and everything but to no avail. I couldn't enjoy myself, it's the only time i've ever even tried to fake an orgasm just so I can go to fucking bed and sleep. She was only 18 so I should have known, I never go for younger girls and I doubt I ever will again. In fact she's the only girl i've had sex with that is younger than me.

Mind you i'm sure back during some of my first experiences I must have been pretty crap for a few of them.

 

[FACE]

*story*

 

[brokenbeans]

Half way through and got a finger up the bum, just didn't do it for me.

 

[Redux]

Glad this thread came up. GAF, I have a problem. I have trouble penetrating my girlfriends vagina. My penis goes limp when I get ready to put it in. I have a good idea why, first time n' all, wasn't comfortable with missionary, extremely nervous, felt a little rushed. But I would appreciate some tips. I can get an erection pretty damn fast, I'm 18. This is just frustrating, and I'm sick of ending off the night with just a blowjob. The girlfriend and I are talking and will continue to try, but I always like to hear GAF's opinion, and tips.

 

[Red]

My first time was kind of shitty. I was fifteen, and my girlfriend and I had left a dance early to be alone. As soon as i got in the upstairs door swung open and my mom came home. So it was like a full three seconds of glory and then panic as i try to hide my boner.

 

[Newline]

Glad this thread came up. GAF, I have a problem. I have trouble penetrating my girlfriends vagina. My penis goes limp when I get ready to put it in. I have a good idea why, first time n' all, wasn't comfortable with missionary, extremely nervous, felt a little rushed. But I would appreciate some tips. I can get an erection pretty damn fast, I'm 18. This is just frustrating, and I'm sick of ending off the night with just a blowjob. The girlfriend and I are talking and will continue to try, but I always like to hear GAF's opinion, and tips.

Seems like you're allergic to the pussy man.

In all seriousness you sure she's not too tight, get plenty of lube and try with that. I've had it before where i've tried to get it in and failed and thus my dick has went limp, so we went back to foreplay and then back for another round. Other than that work your way around the karma sutra till you find one that works.

 

[Opus Angelorum]

Jo Shishido's Cheeks
Had the worst sex ever
(Today, 04:50 PM)
Quote

@Redux try using a penis ring, and lots of foreplay if you're not already.

 

[Manmademan]

This girl I dated right out of HS.

We'd been going out for about 3 months or so, and she invites me over to watch some movies. Well, I always know "movies" equals "time to fool around!' so I'm game. I go over, we're starting to get hot and heavy, and I start the fun game of "lets see how far I can go." Before I know it, we're both in our birthday suits, I'm 5' tall laying down, and she's all over me.

Then I start to hear sounds from the next room over. Its clearly moaning, her parents were going at it. Like really going at it. But the thing is, its almost like she's more into it now that her parents are going at it. She starts moaning real loud, even though we hadn't even done anything yet. I try to get my mind focused, but then I hear her dad yell something, and she literally grabs my head and tries to force me to eat her out.

Her dad walks up to the door, and he's standing there for a good minute or so. I'm soft as can be now, she's fingering herself and trying to get my engines going again, and moaning like crazy. All the while, her dad continues to stand at the door. I shove her hand away, throw my clothes on, and go out the window.

yeah, I had something similar with a girl I dated in college, sorta.

She lived with her parents (I had a house off campus, but it was about 150 miles from her- we saw each other on weekends, summers, or whatever) who were supposedly totally cool with their little girl being nailed while they were home. So, ok whatever, I'm game.

She of course is loud as hell, so there's no mistaking what's going on there every time i'm over, which is pretty frequently, with fairly long sessions.

What I didn't know was that the mother and father were having some "issues" re: sexual intimacy, dysfunction, whatever- so be being over there was not helping the relationship- sort of grinding their nose in the fact that their sex life was terrible. The reception in that house got progressively weirder throughout the relationship because of it.

 

[InvincibleAgent]

Glad this thread came up. GAF, I have a problem. I have trouble penetrating my girlfriends vagina. My penis goes limp when I get ready to put it in. I have a good idea why, first time n' all, wasn't comfortable with missionary, extremely nervous, felt a little rushed. But I would appreciate some tips. I can get an erection pretty damn fast, I'm 18. This is just frustrating, and I'm sick of ending off the night with just a blowjob. The girlfriend and I are talking and will continue to try, but I always like to hear GAF's opinion, and tips.

Maybe your partner needs to adjust her style. Have you tried making the environment more romantic?

 

[brokenbeans]

Glad this thread came up. GAF, I have a problem. I have trouble penetrating my girlfriends vagina. My penis goes limp when I get ready to put it in. I have a good idea why, first time n' all, wasn't comfortable with missionary, extremely nervous, felt a little rushed.

You just gotta keep playing with it and make as much contact with her as possible, kiss her, play with her or even talk dirty.

Anything to keep it steamy.

 

[dankir]

So this girl I was with finally granted me permission for some anal lovage.
I'm warming up her ass with a vibrator, slowly pushing it to and fro with my left hand whilst playing with her pussy with the right, two fingers in and my thumb working her clit.
She's getting very excited by what my right hand is doing, so I momentarily lose focus of the careful actions of my left hand.

"Ploop."

The vibrator disappears up her ass.
No biggie I figure, I can just dig it out.
So I reach in deeper with my left hand whilst stopping what I'm doing with my right.

"What are you doing?"
".....Oh nothing just grabbing this thing."
"What!?"

She leaps up off the bed and begins to panic. I sit her back down, explain, make a couple of jokes and begin my second excavation attempt.
The problem now is between her getting up and sitting back down it's become lodged in at a strange angle and seemingly won't come out.
I pull firmly.
A sudden warm sensation.
Blood.
Lots of blood.

She runs to the toilet, leaking blood over my cream carpet whilst I run after her beginning to freak. I don't like the sight of blood.
She sits on the toilet and begins having what sounds like a very heavy, manly piss.
I look into the toilet and it looks like a prop bucket from Carrie.
So much blood.
I'm trying my hardest to pull this vibrator out but it won't budge.
The blood is making my attempt to get a decent grip on it difficult.
She's crying.
I suggest going to hospital to remove it and she cries more, shouting at me for thinking of putting her in the situation of explaining to the doctor what's wrong.

After a huge amount of blood (repeated flushes were needed), tears and struggles I finally wrestle this vibrator from her ass.
It's still on and vibrating happily.

The downside is this experience has put me off from ever attempting anal sex again.
The upside is I kept the vibrator and gave it to her as a gift a few months later.
She smiled.

Oh come on! Now you're just being silly :S

 

[Übermatik]

Glad this thread came up. GAF, I have a problem. I have trouble penetrating my girlfriends vagina. My penis goes limp when I get ready to put it in. I have a good idea why, first time n' all, wasn't comfortable with missionary, extremely nervous, felt a little rushed. But I would appreciate some tips. I can get an erection pretty damn fast, I'm 18. This is just frustrating, and I'm sick of ending off the night with just a blowjob. The girlfriend and I are talking and will continue to try, but I always like to hear GAF's opinion, and tips.

If it's too tight, that may put you off. It has me in the past. Try to get her more in the mood too, and lube up if need be. Also dress like a dinosaur. Works like a charm for me, every time.

 

[Willkiller]

So this girl I was with finally granted me permission for some anal lovage.
I'm warming up her ass with a vibrator, slowly pushing it to and fro with my left hand whilst playing with her pussy with the right, two fingers in and my thumb working her clit.
She's getting very excited by what my right hand is doing, so I momentarily lose focus of the careful actions of my left hand.

"Ploop."

The vibrator disappears up her ass.
No biggie I figure, I can just dig it out.
So I reach in deeper with my left hand whilst stopping what I'm doing with my right.

"What are you doing?"
".....Oh nothing just grabbing this thing."
"What!?"

She leaps up off the bed and begins to panic. I sit her back down, explain, make a couple of jokes and begin my second excavation attempt.
The problem now is between her getting up and sitting back down it's become lodged in at a strange angle and seemingly won't come out.
I pull firmly.
A sudden warm sensation.
Blood.
Lots of blood.

She runs to the toilet, leaking blood over my cream carpet whilst I run after her beginning to freak. I don't like the sight of blood.
She sits on the toilet and begins having what sounds like a very heavy, manly piss.
I look into the toilet and it looks like a prop bucket from Carrie.
So much blood.
I'm trying my hardest to pull this vibrator out but it won't budge.
The blood is making my attempt to get a decent grip on it difficult.
She's crying.
I suggest going to hospital to remove it and she cries more, shouting at me for thinking of putting her in the situation of explaining to the doctor what's wrong.

After a huge amount of blood (repeated flushes were needed), tears and struggles I finally wrestle this vibrator from her ass.
It's still on and vibrating happily.

The downside is this experience has put me off from ever attempting anal sex again.
The upside is I kept the vibrator and gave it to her as a gift a few months later.
She smiled.

Bravo

 

[Opus Angelorum]

Also dress like a dinosaur. Works like a charm for me, every time.

Is this some costume fetish you have?

 

[threetri333]

The worst sex is not getting one

 

[Red]

The worst sex is not getting one

Not getting one sex?

 

[brokenbeans]

If it's too tight, that may put you off. It has me in the past. Try to get her more in the mood too, and lube up if need be. Also dress like a dinosaur. Works like a charm for me, every time.

A blob of lube would do the trick.

 

[Atramental]

The worst sex is not getting one

That 1 sex is very illusive.